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114618

Sigma-Aldrich

Isatin

97%

Synonym(e):

2,3-Indolindion, Isatine, NSC 9262

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5 G
€ 33,30
100 G
€ 35,60
500 G
€ 112,00

About This Item

Empirische Formel (Hill-System):
C8H5NO2
CAS-Nummer:
91-56-5
Molekulargewicht:
147.13
Beilstein:
383659
EG-Nummer:
202-077-8
MDL-Nummer:
MFCD00005718
UNSPSC-Code:
12352100
PubChem Substanz-ID:
24847187
NACRES:
NA.22

€ 33,30

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Qualitätsniveau

100

Assay

97%

Form

powder

mp (Schmelzpunkt)

193-195 °C (dec.) (lit.)

Löslichkeit

boiling water: soluble
diethyl ether: soluble
soluble

Funktionelle Gruppe

ketone

SMILES String

O=C1Nc2ccccc2C1=O

InChI

1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11)

InChIKey

JXDYKVIHCLTXOP-UHFFFAOYSA-N

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Verwandte Kategorien

Anwendung

Isatin can be used as a reactant to prepare:
  • Phthalazinone derivatives.[1]
  • Spirooxindole derivatives.[2]
  • Agents against multidrug-resistant cells expressing P-glycoprotein.[3]
  • Thiazolidinones spiro-fused to indolin-2-ones as potent and selective inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase B.[4]
  • Triazole-isatine compounds as potential antibacterial and antifungal agents.[5]
  • Biologically relevant scaffolds such as spiro[indole-thiazolidinones].[6]

It can be a reactant for:
  • Cascade reactions with heterocyclic ketene aminals.[7]
  • Knoevenagel condensation reactions.[8]

Isatin can also be used as a chromatographic spray reagent for amino acids, and also as a reference material in the preparation of indigo and Maya Blue. It is responsible for the yellow color exhibited by the "Maya Yellow" pigment.[9]
Isatin undergoes Pd(II)-catalyzed C-H addition by direct sp2/sp3 C-H bond activation to form 3-substituted-3-hydroxy-2-oxindoles[10]. Isatin derivatives (bis-Schiff base) are synthesized by the condensation of the natural or synthetic isatins with hydrazine[11].

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 1

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
0000432504
0000432504
0000358083
BCCL3419
0000336949

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7-Fluorindol-1H-2,3-dion 96%

Sigma-Aldrich

679119

7-Fluorindol-1H-2,3-dion

Novel Synthesis of Some Phthalazinone Derivatives
Mahmoud, M. R.; et al.
Chin. J. Chem., 29, 1446-1450 (2011)
Fuchao Yu et al.
Organic letters, 13(18), 4782-4785 (2011-08-19)
A concise and efficient route for the synthesis of highly substituted imidazopyrroloquinoline derivatives by simply refluxing a reaction mixture of different types of isatins and heterocyclic ketene aminals (HKAs) by acetic acid was developed. This method is suitable for combinatorial
Ozil, M.; et al.
J. Chem. Res. (M), 35, 268-268 (2011)
Versatile three component procedure for combinatorial synthesis of biologically relevant scaffold spiro[indole-thiazolidinones] under aqueous conditions
Dandia, A.; et al.
Green Chemistry, 13, 1852-1852 (2011)
Gang-Wei Wang et al.
Organic letters, 15(20), 5270-5273 (2013-10-05)
The first Pd(II)-catalyzed C-H addition to isatins by direct sp(2)/sp(3) C-H bond activation for the construction of 3-substituted-3-hydroxy-2-oxindoles is reported. The bidentate nitrogen ligands were found to promote this reaction. Specifically, the preliminary bioassay indicated that 3-(5-chlorobenzoxazole)-3-hydroxy-N-benzyl-2-oxindole (2w) is a
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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